


Sam Winchester: Assisting Love-Struck Dumbasses Since 2009

by PrepareToBeMildlyEntertained



Category: Supernatural
Genre: Declarations Of Love, Fluff, Humor, M/M, Matchmaker Sam, Misunderstandings, Sam fucks up a lot, but tries his best
Language: English
Status: Completed
Published: 2015-04-04
Updated: 2015-04-09
Packaged: 2018-03-21 03:54:29
Rating: Teen And Up Audiences
Warnings: No Archive Warnings Apply
Chapters: 2
Words: 7,490
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/3676407
Author URL: https://archiveofourown.org/users/PrepareToBeMildlyEntertained/pseuds/PrepareToBeMildlyEntertained
Summary: <blockquote class="userstuff">
              <p>“I’m in love with Dean.” Sam sits frozen in place. His brain isn’t working properly and Castiel is just staring at him that way he does, which bothers everyone but Dean. Angel-of-the-Lord Castiel has just declared that he’s in love with Sam’s brother and there is no appropriate way to respond to an announcement like that.</p>
            </blockquote>





	1. For Shocking Declarations of Love, Press 1

**Notes for the Chapter:**

> I don't know how this even happened. I love seeing Dean/Cas from Sam's perspective. Sam's sort of a fuck up but he means well. Also, Cas and Dean are bad at communicating. Takes place mid-season 5.

“I’m in love with Dean.” Sam sits frozen in place. His brain isn’t working properly and Castiel is just _staring_ at him that way he does, which bothers everyone but Dean. Angel-of-the-Lord Castiel has just declared that he’s in love with Sam’s brother and there is no appropriate way to respond to an announcement like that. Sure, he’d suspected. Very few people tolerate Dean’s mood swings and generally abrasive personality, and Castiel had gone above and beyond in the toleration department. Apparently, very far above and beyond. And now he just keeps staring.

“Um,” Sam says. He glances at the door to the motel room, waiting for Dean to burst in and maybe save him from having this conversation. They’re in the middle of the apocalypse, after all. There are things to be done. But the door stays closed and Sam swallows thickly.

“Are you alright, Sam?” Castiel asks. It’s the exact same tone of voice he just used to declare his love a few moments ago and Sam almost wants to laugh. Or possibly cry. He does let out one breathless huff, but it sounds strangled more than anything. Castiel’s brows draw together.

“I’m fine,” Sam manages to get out. “Just fine.” He takes another breath. An Angel of the Lord (although there was no telling how much longer that title would even apply) in love with his brother. That’s just about perfect. And an angel in a male body at that. Sure, Sam’s had his own suspicions about Dean as well, he just also knows Dean will never admit to anything, not even to himself. He’s gonna play overly butch for the rest of his natural life. And beyond, since neither of them really have _natural_ lives these days.

“I was hoping for advice on how to proceed,” Castiel says. He finally looks slightly uncomfortable, by which Sam means he looks like he’s constipated. Maybe he is. Emotionally speaking, of course. He would assume that’s just the kind of thing that happens being in love with Dean. He glances at the door again.

“Cas,” he begins, hesitantly, “why are you talking to _me_ about this?”

“You are Dean’s brother,” Cas says, like that’s obvious. And it probably is, but.

“Right, but… I’m an abomination, remember? I thought you didn’t really like me,” Now Sam is even more uncomfortable. He’s been unsure of how to proceed since Cas popped in and asked to speak to him privately, long before he was asked to give _love advice._

“Dean cares about you deeply,” Castiel says, like he’s working through a math problem. “And I care deeply about Dean. And so you are my friend.” He nods like he’s explained it, though it seemed hard for him to actually get out.

“My friend?” Sam asks. This conversation is already too much. He shouldn’t have asked.

“Of course,” Castiel says. Sam rubs his forehead. Somewhere in his brain he’s really flattered.

“Alright. Well, that’s good, I guess,” he says. Cas inclines his head in agreement. It’s worse than talking to Dean about this stuff. Which is probably a good sign, Sam thinks. Except it isn’t. Because Dean’s emotional constipation is going to keep him from ever accepting that what he wants might have a penis.

“So, do you have a suggestion for how to proceed with Dean?” Cas asks. God, it sounds like he’s discussing a business transaction. Like Sam owns Dean and has to give Castiel permission to move forward, which is all matter of fucked up. Sam isn’t Dean’s father, for Christ’s sake.

“Look, Cas,” Sam says, hesitantly. He doesn’t get to finish.

“You feel that Dean might not share these emotions.” Cas says. It isn’t a question, but Sam nods anyway. Castiel nods back. “Thank you for assisting me.” Sam scoffs a bit.

“I didn’t do anything,” he says. Cas shakes his head, still looking awkward as hell.

“You gave me the information I needed to know,” he says. “I may, perhaps, attempt to alter Dean’s feelings now.” Sam stands up quickly.

“What, like messing with his head?” he demands. Sure, Dean trusts Cas, but Sam isn’t totally on that train yet. He’s still an angel. And, up to this conversation, he hasn’t been fond of Sam. Castiel tilts his head curiously.

“Of course not,” he says like it’s obvious and he is explaining to a dull child. “I meant that I could attempt to persuade Dean to fall in love with me by enacting a series of human behaviors.” Sam’s brain takes the time to restart before he can respond. It is such a full restart that Sam wonders if Cas can hear the little start up noise once the brain turns back on.

“Oh,” he says. “Like flirting?”

“I believe that is the colloquial term,” Cas says. Sam’s mouth opens and closes and then opens again.

“I don’t know how great an idea that is,” Sam says. Cas inclines his head.

“I thank you for your advice. It is very valuable,” and then he’s gone with the sound of flapping wings. Sam collapses back into his chair and tries to process. With Dean, conversations about emotions usually leave him frustrated, but this is entirely knew.  This is straight up, muddle-brained bafflement. A few minutes later, Dean bursts through the door holding a white bag that has grease seeping through the bottom.

“How’s research?” he asks as he dumps the food on the table. Sam looks at the bag.

“Fine,” he says. Dean looks at him oddly.

“Not gonna bitch about healthy food, Samantha?” Sam shakes his head.

“Nah, it’s fine,” he says. He tries to let the conversation drift from his mind but, no matter how hard he tries, can’t quite manage it.

 

* * *

 

Castiel pops into their car as they cross the border from South Dakota to Nebraska. Dean swerves in surprise, then rights the car and begins to bitch.

“Jesus, Cas, how many times I have to tell you not to do that?” he asks. Sam swallows. Sure, this is the first time they’ve seen Castiel since their _Conversation_ (big capital C) but that probably doesn’t mean anything. And yes, he did say that flirting might be a bad idea, and Castiel seemed like he listened. So this probably isn’t about that. Probably.

“Hello, Dean,” he says from the backseat. Dean’s lip twitches upward at the familiar greeting and Sam tries not to burst into flames.

“Hey, Cas,” Sam says weakly.

“Hello, Sam,” Cas responds. Dean rolls his eyes good-naturedly at the clumsiness of the exchange.

“So, what’s up, Cas?” he asks. Sam sucks in a breath. This is it. Job or flirting?

“I thought perhaps I would check in and see how you are,” Cas says. Sam sighs heavily. Flirting, then. This shouldn’t be awkward.

“Missed my pretty face?” Dean asks with a wink. Sam begins a prayer that mainly goes, _Why, God? Why?_ This prayer goes on a loop. For several miles. Maybe they don’t have a great relationship with the big guy right now, but he has to have some kind of mercy, right? The apocalypse? Fine. But angels attempting to flirt with his emotionally stinted brother? That’s just cruel and unusual.

“Yes,” Castiel says. Dean laughs like it’s a joke, despite the fact that he _knows_ Castiel doesn’t make jokes. He must _know._ Right?

“Well, we have another three hours of driving ahead of us,” Dean continues. “But you’re welcome to stick around.” Sam probably melts a little bit. He’s not sure. He doesn’t actually remember the rest of the conversation because he allows his brain to shut down. He has a lot of memories in his head he would rather not have, and if he can block the uncomfortableness of this exchange, he will do so willingly and with enthusiasm. So, when Cas disappears with the flap of wings an hour later, Sam is shaken from something like a waking dream and Dean smacks his arm.

“Dude, you tired or what?” he asks.

“Huh?” Sam tries. His brain is still foggy from adamantly refusing to listen to the car conversation. Dean rolls his eyes.

“You just stared out the windshield for like an hour with this glazed look in your eyes,” he says. “So, you tired or do you just hate Cas now?” Sam swallows around a lump in his throat.

“Nah, just tired I guess,” he says. He thinks about Cas saying they were friends and curses every god he’s ever read about before he continues. “I don’t hate Cas. He’s, uh, weird. But he’s a cool guy.” Dean huffs.

“Yeah, weird definitely fits,” he says. On the radio, the song switches over to  _Is This Love?_ and Sam looks at the sky in disgust for good measure. Honestly? Whitesnake? He expects Dean to turn it down but to his surprise the dial goes untouched.

“You seem to like him a lot,” Sam continues, so awkward he feels it in his bones. “I mean, you don’t like a lot of people, so.” Now Dean shifts in his seat.

“Yeah, well, he’s a weird dude,” Dean says. “He’s a useful guy to have in your corner.”  Of course. Emotionally constipated brother. He’d actually forgotten for half a second there. He rolls his eyes internally.

“I mean, it’s more than him being useful,” Sam says. “You guys are, like, friends.” Dean huffs and honest to god _turns up the song_ instead of responding. It’s when he starts muttering under his breath the lyrics, ‘is this love that I’m feeling?’ that Sam almost jumps out of the car.

Hours later, when Sam is the one out on the food run and Dean is back in the room on book duty, Cas flaps his ass back into the car with a considering look on his face. Sam jumps. He is parked, so at least he doesn’t wrap Dean’s precious car around a telephone pole but he still feels that internal annoyance that Dean must when Cas shows up without warning. Except that Dean never shows that annoyance for long. It’s like… feigned annoyance masking amusement. Even when Dean is annoyed at Cas he isn’t actually _annoyed_ at Cas. Fucking typical.

“Jesus, Cas,” Sam mutters. He finishes setting the bag of food down between them. Cas is sitting in the front seat, looking out the windshield.

“I think that my attempts in persuading Dean to feel affectionate towards me were somewhat successful,” he says without a hello. Only Dean gets the hello. Sam pinches his nose.

“Cas, I’m sorry, but my brother is an oblivious ass,” he says. “I wish I could tell you differently but…”

“You still feel that he won’t ever return my feelings?” Cas says. He turns to squint at Sam. When Sam opens his mouth to respond, Cas holds up a finger to indicate he is thinking and Sam’s jaw is left partially open until he snaps it shut in annoyance. He turns the key in the ignition and beings to pull out of the parking lot. After Sam pulls into the street, Cas makes a noise like an epiphany.

“What?” Sam asks. He pulls to a stop at a red light and turns to look at the angel next to him.

“Dean often has a problem feeling he is worthy of affection,” Cas says. Sam’s eyes go past his hairline and all the way to the back of his neck.

“Um, yeah?” he says. It’s true. Dean has the self-confidence of a sea sponge. Actually, how self-confident are sea sponges? He could be wrong. Maybe they were really full of themselves. How was he to know? Getting off topic. He tries to refocus on Cas, who has screwed up his face in thought.

“If Dean doesn’t feel he is worthy of love, he will never feel that he can love me,” Cas says. After a long moment Sam nods. The light turns green and he starts driving again. He doesn’t say anything so Cas continues. “I just have to make him see that he is worthy of love. I have known since the moment we first met Dean had a low opinion of himself. I did not take this into account in my attempts to win his affections. Thanks you for your assistance, Sam.” And then he’s gone again and Sam thumps his hand on the steering wheel for good measure.

“He won’t love you because you happen to have a dick!” Sam shouts into the empty car. Cas’s appearances were so fleeting and odd that he felt he hadn’t had the chance to say it out loud yet, but Jesus, the guy needed to hear it. Dean just wasn’t going to reciprocate. Dean the one-night-stand guy. Dean the manly man. Well, except for that one time with the siren but that was just a brother thing. Sort of. Right? Whatever.

Sam turns the car into the motel parking lot and rapidly pulls into a parking space. For a minute after the car is off, Sam just sits staring at the wheel. Was this his life now? Cas showing up when Dean wasn’t around to ask for love advice like he was Dear fucking Abby while Dean played like he didn’t care? Sam smacked his head down on the wheel of the Impala and then grabbed his bag of food. He walked into the motel room and Dean immediately turned to him.

“Alright, so I think I know what we’re looking for…”

 

* * *

 

Dean’s been acting weird. He has been acting very weird. Alright, maybe Sam doesn’t have the best baseline after juicing up on demon blood again, but that wasn’t even his fault. That was Famine’s goddamn fault. Fucking apocalypse. Except that Dean’s definitely acting weird. Especially after all that shit with Famine. First, he gives Cas food. Gives up his own food to someone. That’s weird enough. But that on top of eating nothing? Sam knows his brother and he knows his brother is not empty, whatever douchebag horsemen might say otherwise.

After the Famine thing, Cas shows up in the motel room. He must listen in to see when the coast is clear because Dean had just barely left to check on a lead. Cas appears literally three seconds after the door closes behind Dean and Sam winces. If he noticed Dean was weird, Cas probably did too.

“Do you think Dean found my consuming of beef to be disgusting?” is the first thing he says instead. Sam honestly doesn’t know how to respond to that. He throws his hands up in the air.

“What the hell are you talking about?” he asks, exasperated. Cas is staring at something that doesn’t exist as he continues.

“I consumed a large amount of beef during this previous case, and I’ve heard that it can be off-putting when a potential lover ingests an above average amount of food,” Cas says like this all makes sense. He’s _heard? Potential lover?_ Sam squints and puts his hands down.

“Are you reading advice columns now?” he asks. Cas nods absently.

“I thought it might be the best way to learn what behaviors to act on,” he says. “I am unfamiliar with many human rituals.”

“Shit,” Sam starts pacing around the room. Why couldn’t Cas have gone to Bobby? Bobby would have taken care of this no problem. Told Cas the honest truth and sent him packing. Probably with a beer for good measure. But Sam was not cut out for this. And he’s been pushed to the extreme.

“Sam? What do you think?” Cas asks, following Sam’s movements around the room with his eyes.

“What do I think about you eating a lot of food?” Sam asks, coming to an abrupt halt.

“Yes,” Cas says. He starts to look suspicious.

“I think Dean doesn’t give a shit if you eat too much!” Sam shouts. He felt it building inside of him and now it all ruptures out at once. His frustrations, his confusion, the fact that he’s not a goddamn couple’s counselor. “I think Dean’s emotionally stunted and that he thinks you’re a cool guy, but he likes women and that’s that. We’re in the middle of a fucking apocalypse, Cas, and you’re busy asking me about Dean like it’s going to change anything!” As soon as it’s all out, Sam regrets it. He sees the fall of Cas’s face, even if it is miniscule. All of Castiel’s expressions were like that, and he was getting better at catching them.

“I see,” Cas says. Sam tries to backpedal.

“No, that’s not... I mean, uh,” he stammers. Cas puts up a hand.

“Thank you for making things clear to me,” Cas says. “I will stop my behaviors immediately. If you would like me to remain absent from future hunts, just let me know.” And he’s gone without the chance for Sam to get another word in. Fuck. Fuck, fuck, fuck. Even in the middle of all this shit, he can’t do this one simple thing for the guy who literally is giving up Heaven for their two sorry asses. Well, probably Dean’s ass more than his. He collapses into his chair and stays there until Dean comes back an hour later.

He walks through the door slowly and closes it carefully. Sam is still in the chair. He looks up and Dean shuffles on his feet, which is weird.

“What did you find out?” Sam asks, bunching up his brows at his brother, who looks majorly uncomfortable. Strange, considering he’d just come from the house of a very attractive, very female, potential witness of a possible poltergeist. For a few seconds Dean says nothing, and then he straightens abruptly and looks Sam dead in the eyes.

“I’m in love with Cas.”

Well shit.

**Notes for the Chapter:**

> Ah, yes, the love-struck dumbasses. Sam puts up with a lot. Stay tuned for more. And let me know if you liked the first chapter!  
> If you all want to go listen to the song Dean was rocking out to, [it's right here](https://www.youtube.com/watch?v=ujnH4yNqL8E).


	2. For Absurd Matchmaking Plans, Press 2

**Notes for the Chapter:**

> Wow! The response I got to the first chapter of this was crazy. I'm so glad you all enjoyed reading a fic I wasn't even planning on writing. I hope you all like the conclusion just as much as the beginning.

“Are you fucking kidding me?” probably aren’t the best words to say first, but that doesn’t stop Sam. Dean gets immediately defensive.

“Hey, fuck you,” he says. “I come in here with a heartfelt confession.” He shakes his head a little and Sam makes a frustrated noise.

“That’s not what I…” he blinks slowly and clears his throat. “You’re in love with Cas?” Dean shifts a bit again, anger starting to fade as quickly as it appeared. He looks spooked, like an animal suddenly caught eating the rosebushes.

“I, well, yeah. Yes. I am,” Dean says. A few seconds of silence goes by as Sam considers the universe and how royally fucked up it is.

“And you decided to tell me this now?” he asks. He doesn’t mean to sound like a bitch but that’s the way it comes out. He doesn’t want to shout _if you just could have told me yesterday_ or _I can’t believe I fucked this up for no good reason_ and barely manages to hold them both in. Dean pulls off his coat abruptly, probably mostly so he has something to do with his hands.

“Yeah, it was, uh, it was the Famine thing,” he says. Ah, well that explains that then. “It wasn’t that I wasn’t hungering for anything, exactly…” He drifts off like he was about to say something else and suddenly decides he would very much not like to say it out loud. So Sam says it for him. Because that’s what good brothers do.

“You were hungering for Cas?” Sam asks. Dean makes a face.

“God that sounds fucked up when you say it,” he sinks his head into his hands at the same time as he sinks into the chair across from Sam. “It’s so fucked up, Sam. I mean, he’s an angel.” Sam waits for the inevitable. But it doesn’t come, so Sam fills it in again.

“And he’s a man,” he says, thinking _why aren’t you making a bigger deal of that bit?_

“So?” Dean asks. Sam’s eyes grow about three sizes.

“ _So?_ ” he asks. Dean looks up and shrugs.

“Yeah, he’s a guy, whatever,” Dean says. When Sam doesn’t respond he continues. “Wait, seriously? I mean. Oh, God. I didn’t think that’s what this conversation was. I thought. Well, I figured. I mean my siren was a _man._ Oh, Jesus.” His head drops into his hands again and Sam just slowly starts to nod.

“Right, no, obviously,” Sam says, trying desperately to ease the situation. He clears his throat. “Men. No big deal for you to love a, uh, man.” _That’s definitely something I figured out a while ago,_ Sam thinks sarcastically but doesn’t add, the pieces clicking into his head in screaming succession. Holy shit, how had he missed it?

“But it’s so fucked up,” Dean continues almost like a whine. “He’s like, you know, Angel Of The Lord Castiel. I’m no one.” Sam actually starts to laugh. He’s had a rough day, sue him. And this isn’t going the way he wanted it to go. His brother basically came out to him and now he’s laughing in his face. God, he needs to sleep. And he needs the apocalypse to be over. And he needs a bottle of whiskey. Dean looks wounded, though, and Sam manages to sober himself up.

“No, Dean, I’m sorry,” he says. “I didn’t mean to do that. It’s been a long day. You’re worried he doesn’t care about you?”

“How could he?” Dean asks lowly. Sam lets out a long breath of air.

“Why don’t you talk to him about this?” he says. Dean looked up at Sam like he’s the stupidest being on the planet.

“Right, just call him up and declare my love?” he scoffs. “And then have him awkwardly say he doesn’t feel _that way_ and watch him flap his ass the hell out of here for good? I think we need him around to deal with the apocalypse before I totally fuck everything up.” Sam nods solemnly, determined to treat this situation more delicately now that he’s almost fucked it up twice. And the fact that he may have fucked the whole thing up permanently already. Shit.

“I don’t know, Dean. I think you should give him more credit than that,” he says. Dean huffs.

“He’s hauled ass out of here for less,” he says. “No, I don’t want to do anything. I just. I don’t even know why I said anything. I just felt like I should or something. Whatever.” He stands up and puts his coat back on abruptly. Sam is so taken aback it takes him a second to catch up and stand.

“Wait, where are you going now?” he asks. Dean marches to the door. He won’t meet Sam’s eyes.

“Out for a drive,” he says. He slams the door as Sam calls out for him but doesn’t come back.

“Shit,” he says. He puts his hands on his hips. Looks like his job as matchmaker was back in effect. Fucking hell.

 

* * *

 

 

When Dean comes back, he doesn’t mention the conversation. And when Sam looks like he’s about to bring it back up, Dean abruptly changes the subject. So, that’s off the table for now. Sam doesn’t know why he doesn’t just tell Dean how Cas feels. Well, except that he does. First, it doesn’t feel like his place to tell Dean. That’s not a by-proxy kind of fact to share. You don’t play telephone with _I love you’_ s. So, there was that.

Also, Sam was pretty sure at this point that Dean wouldn’t believe him. Hell, Cas had told Sam himself and he was still a bit incredulous. He’d seen the way Cas looked at his brother first hand and hadn’t believed it. But Dean? No way would he believe Cas loved him. Even if Cas actually told Dean to his face he might not believe it. But that was exactly the scenario Sam was going to have to attempt to make happen. If he was going to be a matchmaker, he was going to have to be a damn good one.

The day after what he will forever call _The Infamous Dean/Cas Fuck up,_ he and Dean drive to Indiana. They’re there for a salt and burn, which shouldn’t take long, but when Dean offers to split up Sam accepts the suggestion with more enthusiasm than is probably necessary. So Dean takes off to talk to a witness and Sam is supposed to check into town records. Only he doesn’t do that. He stays in the motel and prays to Cas. For extended periods of time.

“Cas, come on,” Sam says, going into the tenth minute of this prayer so far. “Don’t do that thing where you only come when Dean prays to you. I need to talk to you.” Maybe it’s finally mentioning Dean instead of apologizing profusely for his outburst but Cas appears in the middle of the motel room, refusing to meet Sam’s eyes.

“Sam,” he says, shortly. Sam takes a breath.

“I was wrong,” Sam says. Cas stiffens and looks up, looking at Sam suspiciously.

“You were wrong?” he asks. It’s got an undercurrent of distrust and Sam figures yeah, he definitely deserves that.

“I was wrong to yell at you like that,” Sam continues. He stands up and crosses to where Cas stands in the room. As it turns out, Cas only has a personal space thing with Dean because he takes a step back as Sam approaches him like a wounded animal. Sam tries not to feel like he fucked it all up for good. Cas is his friend. _Was_ his friend? Is. He’s going to make sure it stays in the present tense. Cas looks down again.

“Ah. You apologize for your outburst. I forgive you. You were only being honest,” he says. He looks like he’s about to fly away again and Sam jumps forward and puts a hand on his arm to stop him. When Cas looks up, he seems miffed.

“Cas, just let me finish,” Sam says. Castiel shakes his arm free but doesn’t fly away, which Sam takes as a good sign.

“I understand that you were just attempting to prevent me from further embarrassing myself, Sam,” Cas says. “I don’t begrudge you for that.” Sam shakes his head, growing frustrated. Dear God, Cas and his brother were fucking _made_ for each other. Cas can talk all he wants about Dean having a low opinion of himself, but he wasn’t going to win the self-confidence award any time soon either.

“No, that’s not what I mean,” Sam huffs. “I was wrong to tell you Dean would never care.”

“You were?” he says. It isn’t a question, really, just the continued suspicion with a hint of the flat tone the angel had a habit of defaulting to.

“Yeah,” Sam says. He looks around and takes a breath. “I don’t think you should give up with him. I think you should… keep trying to convince him.” He can’t say the actual word out loud. He can’t tell an angel to flirt with his brother. He’s been through a lot. Literally died once. Almost died a whole lot of other times. But he can’t possibly use the word _flirt_ in conjunction with what an angel should do with his brother. Every person has their limits. While he has this breakdown, Cas seems to consider.

“You feel I should continue using human mating rituals to convince Dean of my feelings?” Cas says and Jesus _Christ_ does he have to spell it all out? Sam barely holds back a wince at _mating._

“Yes,” he chokes out. A small smile stretches across Cas’s lips and he ducks his head in something that might almost be called bashfulness. It’s just about the most human Sam has ever seen him look.

“Thank you, Sam,” he says, and then flaps out. Sam lets out a huge breath and shakes his head. If he understands Cas at all, the angel is headed to his brother right now. Which means the pieces are in place. Time to set up for the final step. How the hell did he get into this?

 

* * *

 

 

Half an hour later, Dean bursts in. His eyes are wide, his shoulders stooped, and he looks a combination of confused and angry.

“Did you say something to Cas?” he asks before he slams the door. Sam slowly looks up from his laptop. He’s sipping a beer, looking as nonchalant as possible. Or at least trying to.

“About?” he asks. He’d rather hear Dean say it again. Just because he’s still convincing himself, to be honest. Dean’s eyebrows draw together in further annoyance.

“About my big gay love confession?” he shouts. Sam stays calm and sips his beer.

“I think you mean bisexual love confession,” he says primly. Dean’s eyes burn a little hotter.

“Whatever! You know what I mean!” he shouts. He comes at Sam quickly and points at him. “Did. You. Say. Something?” Sam shrugs his shoulders.

“Haven’t seen him,” he says. He stands up when Dean deflates. Then takes a step forward and trips over the motel kitchen table, spilling beer all down the front of Dean’s fed suit. “Oh, shit!”

“What the fuck?” Dean takes a huge step back and gestures at the liquid-covered suit. “Hey, sasquatch, control your gangly-ass legs.” He shakes his hand and a few drops of beer fly off. Sam puts his bottle down and starts wiping Dean’s shirt with his bare hands.

“Oh, God, I’m sorry,” he says. Which is when the ink that _somehow_ spilled on his fingers earlier gets all over Dean’s white shirt. Dean shoves him away abruptly.

“Alright, hands off,” he says. “First Cas asking about my fucking _interests_ and now you’re acting like you learned how to walk yesterday. I’m taking a damn shower.” He storms off into the bathroom and slams the door. Normally, Sam would be pissed enough at his brother for the outburst that he’d drive down to a bar for a few hours. But luckily the yelling and clumsiness was just phase one. He waits until he hears the shower turn on before he moves to the place in the room farthest from the bathroom door and calls Cas again.

“Cas, something happened. It’s about Dean,” Sam says. He steels himself again. Luckily, he knew this part should involve less yelling than his conversation with Dean had. Cas appears within seconds, a wild look in his eyes.

“What happened?” he demands. Sam crosses his arms.

“What did you say to Dean?” he asks. Cas straightens and looks back and forth, seeming to check if the coast was clear before he started to speak.

“I asked him about what he likes to do in his free time,” he says. “I saw once that people enjoy being asked about their interests. When he told me he liked knitting, I suggested maybe he could teach me sometime because I also read that people like engaging in activities they enjoy with others. But it turns out he may have been joking. What happened to Dean?”

“Well, you did,” Sam says. He licks his lips. “I think you made some progress. And I have an idea.” He almost rolls his eyes at his elaborate giddiness. Might as well sell the hell out of this, if it’s gonna even sort of work. At the very least, Cas seems to cheer at the news.

“You think Dean might change his mind?” he asks. Sam hears the shower in the bathroom turn off. Fuck, he forgot how quickly Dean can take a shower when he wants to. Sure, half the time he takes showers like there’s no tomorrow, but on the occasions that Sam needs a bit of time?

“Yeah, exactly,” Sam says. He glances at the door and lowers his voice. “I think you should meet us for dinner. At this place in town. It’s called Mina’s. Meet us there in like fifteen minutes? Make it a table for two, though.” He glances at the door again, willing Cas to get it and go. Luckily, for once in this whole goddamn disaster, shit actually goes well.

“Of course,” Cas says. Probably the idea that he was making progress was making him move faster. Mentioning Dean did always have a tendency to get his head in the game more quickly, when Sam thinks about it. There’s a flapping noise and Cas is gone, just in time for the bathroom door to open. Dean walks out wearing a towel and immediately starts digging around in his duffle for jeans and a shirt.

“Hey,” Sam starts, turning in place from where he’d been talking to Cas. “Sorry about your suit. I’m a little scattered. And a lot hungry.” Dean looks up from his bag, squints a bit, then shakes his head.

“No big deal,” he says. Sam resists the urge to snort. Right, no big deal at all, Dean. Didn’t even sort of overreact when you burst in here a bit ago. “Let me get dressed and we can head to a bar or something.”

“Actually,” Sam interjects. Dean is about to go back into the bathroom and he stops, hand on the door, looking at Sam in a way that says he’s still annoyed but doesn’t really want to acknowledge it. Sam has seen that face a lot of times. “I was thinking we’d head to this restaurant I saw when we drove in. Get some decent food for once.”

“Yeah, sure,” Dean agrees like he’s waving Sam off. He disappears back into the bathroom and Sam lets out a breath. God, this was terrible. Why did he decide to do this? There was no way he was going to fucking Parent Trap these two idiots into anything. He rubs his hands on his jeans and, as he’s been doing a lot recently, tries to keep from melting into a puddle on the floor. Dean reemerges from the bathroom, all clothed like a real boy.

“Here, you know where this place is,” he says. He grabs the keys off the table and tosses them to Sam easily. “You drive.”

 

* * *

 

 

Mina’s is a nice place. Sam is pretty sure it is, anyway. From the glance he got as they drove by yesterday. Alright, so he has no idea. But he can hope. It’s sort of pathetic that this is the kind of confidence he’s working with on this plan, but there you have it. He pulls the car into a space and he and Dean get out at the same time, Dean giving the restaurant an appraising look.

“Not bad, Sammy,” Dean says. Sam smiles but it feels a little frantic. He has no idea what his face looks like. Probably not normal. Definitely not normal, based on the way Dean looks at him.

“Well, let’s head in,” Sam says, trying not to sound like he’s being strangled. The restaurant, as it turns out, is very nice. It’s got low lighting and the walls are a dark shade of red. There are a few couples leaning across the table to talk to each other. And Sam sees Dean notice Cas almost immediately, the angel sitting primly in the corner at his own little table. It has a small candle and two place settings. Sam actually _feels_ Dean’s mood darken.

“Sam,” he says deeply. Sam goes for innocent, but he’s sure it probably comes across more like he has a gun to his head.

“What?”

“What is Cas doing here?” he asks, voice lowering even more. In the corner, Cas looks over at them and the little bit of almost-happiness that had sat on his face earlier fades into concern. He raises a shy hand and waves.

“What, angels don’t eat?” Sam asks, voice cracking. Dean spins on him.

“No, Sam, they don’t!” he shouts. A few heads turn to look at them and Sam gives a few quick apologetic smiles. The hostess raises a displeased eyebrow in their direction and Sam swallows. Yeah, he hadn’t really thought the Parent Trap scenario would play out perfectly. One could dream.

“Maybe he just decided to pop by,” Sam says, swallowing. Dean scoffs and shakes his head, looking ready to tear someone’s face off. Probably Sam’s.

“You told him, didn’t you?” he says. Sam shakes his head adamantly. He sees Cas’s eyebrows furrow across the room as the angel stands.

“No, I didn’t tell him anything, Dean,” he tries to assure. Since it was one of the first true things he’d said in the last half hour or so, he thought his sincerity would come through and calm Dean down. But he was definitely wrong.

“Fuck you,” Dean says. Sam thinks he almost turns around to look at Cas, but then he seems to reconsider and storms out without a glance. Cas quickly crosses the restaurant and gets to Sam as the hostess begins asking them to leave. Cas talks over her.

“What happened?” he asks. He sounds almost sorrowful, and Sam wants to punch himself in the face. He grabs Cas’s sleeve and pulls him out of the restaurant with another apologetic wave to the hostess, who just scowls at him. Weird, he can usually smile his way out of shit like this. Maybe the stress is affecting him. Once they are outside, Sam flips Cas around.

“I’m really sorry, Cas, I may have messed up slightly,” he says. Cas’s eyes turn downwards in sadness.

“But I thought my efforts were working,” Cas says. He sounds so damn disappointed Sam wants to take him to a petting zoo or something to try to cheer him up. Maybe adopt the poor guy a kitten. Something fluffy would probably improve his mood. Possibly. Sam really does not have any kind of expertise in this at all.

“This wasn’t your fault,” Sam assures him, putting a hand on Cas’s shoulder. Unlike last time, Cas doesn’t shrug away from the contact. “Dean’s mad at me, not you.” Cas’s shoulder stiffens and his eyes turn into slits as he squints, suddenly suspicious. Sam starts at the change.

“Did you tell Dean?” he asks. That’s it. What’s the point anymore? He should just explode and be done with it. Not in a ‘yell at Cas, fuck everything up’ kind of explosion. An actual explosion that involves him ending up in a lot of tiny pieces where he won’t have to deal with this damn problem anymore because these two are so obviously fucking perfect for each other and there is no way Sam is ever going to—

“Tell Dean what?” Sam’s eyes widen and he sees Cas’s do the same as they hear the voice. They both slowly turn to see Dean standing not far from them, sitting on the hood of the still-parked Impala. Sam is suddenly very aware of the feeling of keys in his pocket. Dean couldn’t storm off the way he normally does: Sam drove.

“Um,” Sam begins, helpfully.

“Uh,” Cas adds, with much more eloquence surely. Dean crosses his arms more firmly and looks between them distrustfully.

“I asked, ‘tell Dean what’? Either of you dumbasses going to fill me in?” Dean continues. Sam glances quickly between the two of them, trying to calculate what words he could use that would cause the least damage. But he can’t think of anything. And he can’t think of anything. _And he can’t fucking think of anything._ And, if Cas’s face is anything to go by, he can’t either. Dean shakes his head like he’s disappointed, but he also just looks damn tired.

“Dean,” Sam starts, but Dean holds up a hand.

“Whatever, Sam,” he says. “Just give me the keys.” Sam sighs but obeys, reaching his hand into his pocket and tossing the keys to Dean all in one movement. His brother is about to pull open the door to the Impala when Cas speaks up.

“I thought he told you that I was in love with you,” he says. Dean’s hand freezes. Sam’s eyes widen to the size of plates and his jaw drops so quickly it almost unhinges before he snaps it shut again. “That I, ah, _am_ in love with you.” It’s like the world is frozen. Sam wants to move, wants to run away, but now that the words are actually out there he’s terrified of moving. What if he breaks some kind of spell and they both go back to never speaking again? He definitely can’t organize anything like the shit that’s already gone down tonight again.

“You,” Dean croaks. He clears his throat and turns slightly so he’s looking at Cas, but he can’t meet the angel’s eyes. “You what?”

“I love you,” Cas says. It’s like now the words are out, they’re easier to repeat. This declaration comes out much stronger than the last one and Sam cheers internally, though he still doesn’t move. Dean shakes his head slowly.

“No, you don’t,” he says. The cheering in Sam’s heart stops and he feels like he is going to slap someone.

“What are you talking about?” Cas asks. Well, demands, really. Dean sighs and finally meets Cas’s eyes.

“You don’t love me,” he says. “You can’t love me. You’re just saying this because Sam can’t keep his damn mouth shut. Don’t embarrass me more than I already am, alright? I don’t need it.” He turns back to the car.

“Sam didn’t tell me anything!” Cas says. He takes a halted step forward and stops when Dean whirls around again.

“Right, so you just happen to come to me the _day after_ tell my brother I love you and declare your love right back to me? That’s fucking likely. Don’t mock me, ok. I’m a big boy. Just leave it alone,” the last sentence comes out sounding so broken that Sam aches for his brother. The big fucking idiot. Both of them.

“You… you love me?” Cas asks in a gasping breath. Oh, that’s right. He didn’t know that. Dean looks at him oddly.  
“Yeah, that’s what Sam told you, isn’t it? That’s why you’re here,” Sam sees the tiny bit of hope building in Dean’s eyes and sends out another prayer into the universe. _For fuck’s sake, just let them figure it out already._

“Sam didn’t tell me anything,” Cas says lowly.

“He didn’t tell me anything either,” Dean replies. Sam feels like saying _hey, still standing right here_! _Glad you both have so much faith in me!_ But considering something actually seems to be happening, he barely contains the words.

“You love me,” Cas says almost reverently.

“And you love me,” Dean says. He takes a deep breath inwards. “Well, that should make this a lot less awkward then.” With that, Dean marches across the little bit of space that separates them and pulls Cas to him in a kiss. Their lips crash violently, and Cas obviously doesn’t have a damn clue how to kiss, but Sam wants to cry a little bit at the way they fall against each other so naturally. He’s still staring at them, a bit misty, when their lips break apart and Dean speaks a little breathlessly.

“Sam,” Cas says in a low voice.

 “Yeah?” he says. Cas doesn’t look at him, just continues to stare at Dean.

“Thank you,” he says. Then he pushes forward and locks lips with Dean again, looking like he is going to shove them both against the hood of the Impala when they vanish with the sound of flapping wings. Sam laughs loudly, suddenly, in a very crazed sort of way. Holy shit. He actually fucking did it. He fingers his keys and gets into the Impala, heading back to the motel in a haze of bliss. Maybe he isn’t so bad at this matchmaking shit after all.

He pulls into the motel parking lot and gets out of the car without thinking. He’s so happy he honestly forgets the fact that if Cas and Dean disappeared from one place, they must have appeared in another. This is something he only remembers when he gets to the motel door in time to hear a moan that brings him screeching back to reality. He leaps backwards and claps a hand over his mouth before he can shout anything. Not that they would hear him, all the sound they’re making.

He sprints all the way back to the car and jumps in before stopping to catch his breath. Well, he did it. He just hadn’t really considered what ‘ _it_ ’ was. But if they were happy, that was what mattered. Sure, there was an apocalypse on, but maybe if the two of them were slightly less emotionally constipated they would be able to figure their shit out. There’s a sudden crash inside the room loud enough that he hears it all the way out in the car and he abruptly turns the ignition on and backs out, intent on driving to the nearest bar and not returning for a good long while. He’s happy they’re happy. Actually, he’s fucking thrilled. But that sure as hell doesn’t mean he has to listen in.

**Notes for the Chapter:**

> Thanks to everyone for reading! Please feel free to leave a kudos/comment. And, if you're interested, follow me on [tumblr](http://preparetobemildlyentertained.tumblr.com/)!


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